Diego ran headlong through the gunfire toward the boats on the beach. “Are you Captain Drake’s?” he cried. He had to get on board. He had heard there were no slaves in England, and if he joined the English they might take him there. He knew some of their countrymen traded in slaves, but he was willing to stake everything on this chance of freedom. Nothing could be worse than staying with his Spanish master. He could not join the runaway slaves in the mountains—he had betrayed them once too often—so Francis Drake was his only hope. “I must join you,” he shouted, “let me aboard.” A bullet whistled past his head in answer. “I have important information. You are in great danger!” Again they shot at him. “Listen! If you don’t take me aboard you will all die.” They fired once more. “There isn’t much time. Let me aboard!” At last they relented, and as his feet hit the deck he felt elated. A handful of English sailors pressed around him. They demanded to know what he had to say. “You must send word to your Captain,” he said breathlessly. “He must retreat. If you do not depart before daybreak you face certain death.” A few men were dispatched to warn Drake and his raiding party. Diego sank to the deck in relief.

We can only imagine the details of the initial meeting of Diego and Sir Francis Drake’s men, but it almost certainly began as a hostile encounter. Who was to know that this African man, when he convinced Drake’s men to allow him on board the ship, would go on to become a key figure in Drake’s history-making explorations?

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Diego—no surname is known—was an African who fled Spanish enslavement to join the English when Francis Drake and his company attacked the port of Nombre de Dios in Panama in 1572. Diego then forged an alliance between the English and the local Cimarrons, Africans who had run away and established their own settlements in the Panamanian hinterlands. This resulted in a successful attack on the Spanish mule train carrying silver across the isthmus of Panama. Diego then returned to Plymouth with Drake, where he lived for the next four years.

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On 15 November 1577, Diego was one of about 170 men who set sail with Drake from Plymouth. The fleet comprised five ships: Drake’s Pelican; the Elizabeth, captained by John Wynter; the smaller Marigold; the provision ship Swan and the Benedict, a small pinnace. Rather than reveal his true intentions, Drake told the crew they were embarking on a trading voyage to Egypt. It would have been hard to persuade men to take ship for a rampage around the world, with the very real dangers that entailed. Nonetheless, the more astute among them might have realized that Drake’s past exploits as a slave trader and privateer—and the presence of 41 guns across the fleet—made it unlikely that this would be a peaceful trading expedition. Diego, given his previous experience of South America and proximity to Drake, may have known the truth.

On board the Pelican, Diego was Drake’s personal manservant, preparing his clothing, serving his meals and running errands. Diego’s experience in long sea voyages would have recommended him as a crew member; and with Drake’s iffy command of the Spanish language, Diego’s fluency in Spanish and English would make him a useful interpreter when Spaniards or Spanish-speaking Portuguese were captured. He could pass as a slave and spy on the Spanish. And should Drake wish to ally with the Cimarrons, Diego could once again be the go-between.

History remembers Sir Francis Drake (1540-1596) as the first English explorer to circumnavigate the globe, but no images remain of Diego, the escaped African slave who became his interpreter and right-hand man. (Credit: Universal History Archive/Getty Images)

On Drake’s circumnavigation voyage, Diego’s skills as an interpreter proved particularly advantageous as the true nature of their mission became apparent. After an initial setback, when heavy storms forced Drake’s fleet to seek shelter in Falmouth harbor for almost a month, they sailed south, catching sight of the coast of Morocco on Christmas Day 1577. Drake then began seizing Spanish and Portuguese shipping off the West African coast.

Having crossed the Atlantic, the fleet reached Brazil in April 1578, then sailed south along the coast of South America before crossing the Magellan straits. By the time Drake rounded Cape Horn in the Pelican, his was the only ship remaining. This was the moment when, according to Francis Fletcher, the ship’s chaplain, the ship was renamed the Golden Hinde, after the personal crest of Christopher Hatton, Lord Chancellor of England, and one of the voyage’s key sponsors.

On 25 November 1578, just over a year after leaving Plymouth, Drake and his crew landed on Mocha Isle, off the coast of Chile. They were desperate for fresh water, firewood and food after their difficult passage across the straits. To their great delight, the island’s inhabitants gave them two sheep, chickens, Guinea wheat (maize) and fruits. Using sign language, the English asked for drinking water. Their hosts told them to return the next day. That night, the mutton and chicken were ‘so sweet, that we longed for the day, that we might have more.’

The next morning, Diego, Drake and ten other men ‘set out with joy’ for the island. This time they were met not with friendship, but with a flurry of arrows ‘so thick as gnats in the sun.’ It seems that the day before, someone had foolishly used the Spanish word agua to ask for water. Overnight, the island people became convinced that the visitors were their mortal enemies. For the islanders were Araucanians, refugees from Arauco on the mainland, which they had abandoned after ‘cruel and extreme dealing’ from the Spaniards. As Diego was fluent in Spanish, he may have been the offender. Two men, Tom Brewer and Tom Flood, who had already gone ashore at the time of the ambush, were captured. Those remaining in the boat were ‘enforced to be butts to every Arrow’—and, by some accounts, darts and stones as well.

The fate of the two captured men, Brewer and Flood, is uncertain. The official account, The World Encompassed by Sir Francis Drake (1628), stated that they were ‘suddenly slain,’ but Francis Fletcher’s earlier notes on the voyage recorded a far more grisly fate. He claimed that when Drake’s men returned, armed, to the island to try to recover the men, they saw them bound and lying on the ground. A crowd of 2,000 Araucanians was dancing wildly around them, while a few cut pieces of flesh from the Englishmen’s bodies and tossed them in the air. The rest caught these ‘gubbets’ and ‘like dogs devoured [them] in the most monstrous and unnatural manner . . . till they had picked their bones, life yet remaining in them.’ This episode reads like a typical account of the cannibalism supposedly practiced by natives of South America and other distant lands, common to the travel literature of the time. And yet the detail is so vivid it is difficult to discount entirely.

Francis Drake’s ship, the Golden Hinde, was the first English vessel to circumnavigate the globe. (Credit: DeAgostini/Getty Images)

According to Richard Hawkins, Diego received more than 20 wounds in the Mocha Island attack. However, Francis’s cousin John recalled that ‘the arrows did not enter the flesh deeply.’ In any case, he was not the only casualty: Drake was hit in the face and Great Nele the Dane died of his wounds within two days. When the injured men returned to the ship, ‘the horror of their bloody state wounded the hearts of all men to behold them.’ They did not have much medical help. The chief surgeon was dead and the other was left behind in the Elizabeth. There was ‘none left us but a boy, whose good will was more than any skill he had.’

Despite his multiple wounds, Diego survived. Although the main text reporting the Mocha island incident reported that he died of his injuries, a marginal note adds that he died near the Indonesian Moluccas, islands which the Golden Hinde only reached 12 months later. It’s not clear how such wounds might take a year to kill a man. It may be that one of his 20 wounds became infected and turned gangrenous, or he could have developed scurvy, which causes old wounds to reopen.

Diego’s survival until November 1579 is corroborated by the testimony of others who saw him aboard the Golden Hinde months after he was wounded at Mocha. The Portuguese pilot Nuño de Silva testified that Diego, whom he mentioned by name, was still aboard when he left the ship at the Mexican port of Guatulco in April 1579. Drake’s cousin listed an African ‘they had brought with them from England’ amongst those who set sail from Guatulco later that month.

Juan Pascual, another Portuguese pilot, also met Diego while a prisoner on the Golden Hinde in the first half of April 1579. He later testified that he’d met two ‘negroes’ on Drake’s ship. One, clearly Diego, spoke Spanish and English, and ‘everyone said that the Englishman had brought him from England.’ The other was ‘seized at sea.’ Pascual also reported that one of these two men, though he could not recall which one, told him that they had ‘made a contract with Francis Drake,’ meaning they were being paid wages, just like the rest of the crew.

This could only have been Diego, who had been with the ship from the outset.